Early Uber advisor Bradley Tusk looks back — and forward — as its IPO fast approaches

Bradley Tusk’s story is well-known by now. A political operative who managed Michael Bloomberg’s successful third mayoral campaign, Tusk soon turned a bonus from his powerful boss into an opportunity that most people can only dream about. He launched his own business to help clients navigate turbulent regulatory waters, and one of his first calls came from Uber. Which paid him in stock.

Tusk has since used some of that wealth to create numerous other businesses, including the venture firm Tusk Ventures, which has more shiny new holdings, such as stakes in the e-scooter company Bird, the insurance company Lemonade, and the online pharmacy company Ro.

We caught up with Tusk today after his return from a New York Met’s game to ask how he’s feeling about Uber’s IPO, what he’s expecting next week and what moments he remembers best from his work with the now 10-year-old company.

TC: Your Uber shares have climbed astronomically over the years. You’d said you were looking to cash out a big part of your stake when SoftBank acquired 15 percent of the company last year. Are you selling the rest next week?

BT: I still have a lock-up, but when that’s over, I’ll sell as it makes sense.

TC: Uber is reportedly offering 180 million shares at $44 to $50 apiece for its public debut, meaning its valuation could top $91.5 billion. How important is IPO pricing?

BT: On the one hand, it’s everything because you’re putting a number out there that’s in some ways subjective, and if it works, you work [as a banker] and if it doesn’t, you don’t. It’s the moment of truth in some ways.

But if you decide, I’d rather price [the offering] at 10 percent less because it will result in a 20 percent increase [right away], that’s not an unreasonable strategy, and as someone who has to wait six months, I don’t mind it at all.

TC: Looking at Uber’s core platform and its “other bets,” where do you expect to see the most growth?

BT: I’d say the other stuff for two reasons. First, Uber Freight could be scaled to a bunch of verticals beyond logistics for trucking. I also think Uber being Uber that they’ll come up with something we don’t know about yet, like they’ve done three times now. And when they do, that will account for a lot of growth.

BT: Yes, because I think autonomous is not any longer believed to be a market where the first [mover] wins. People understand that the cost of development is higher than anyone ever anticipated. Autonomous vehicles will be developed in different ways by different people and [these players] will all be adding partners and spreading risk and bringing in additional resources . . .

TC: And will they work closely with cities? Can Uber gain traction with its self-driving technologies if it doesn’t? Can any of these companies?

BT: On the one hand, Uber has more experience dealing with city government than anyone else working on autonomous vehicles, and that counts for something. We saw what happened when Amazon tried to deal with local politics in New York.

Once you scale, I think you’ll have federal pre-emption. It’s one thing for every city, town and state to set their own traffic rules, but if we’re in a moment where some cars are autonomous and some aren’t and we have arbitrary differences — say you realize you’re in New Jersey and so have to have your hands on the wheel — [it’ll be a mess]. If Congress were a rational, functional, deliberate [governing body], it would [start figuring this out].

TC: Assuming it doesn’t, how much does that slow down these efforts?

BT: If it doesn’t, that’s when the notion of dealing with cities and states really comes into play. The downside is even if you had everyone [in local government] working with you, the odds of them adopting the same rules [across cities and states] seems unlikely, but these companies may have to make it work, at least as a backup.

TC: Have you stayed in touch with Travis?

BT: Yes.

TC: What do you think of his current plans to turn more empty or underused real estate into places for on-demand services, like fully equipped kitchens that restaurants can use to fulfill takeout demand?

BT: I think it’s really interesting, especially the food piece, where you have these two trends moving along at the same time. First, people seem not to want to cook as much as they used to, and I think that’s a full-on change in society, not a fad or a blip. Also, restaurants’ margins are really low and the cost of operating restaurants is really high. So I think what we’ll see are more restaurants that maintain one physical restaurant as almost a branding exercise, a loss leader that helps them build their name — then they’ll make money on delivery.

TC: Are you investing in these types of businesses, too?

BT: I don’t think Travis is raising money, as I understand it. [Laughs.] But I suspect that at some point, we’ll do some work with Travis one way or another.

TC:Lyft and Uber use different methodologies to account for “Active Riders.”Uber defines it as a unique consumer who completes a ride share or rents a scooter or has an Uber Eats meal delivered at least once in any given month, then it averages that number of monthly users for the quarter. Lyft just defines active riders as all riders who take at least one ride on its platform during a quarter. Which better represents engagement, in your view?

BT: You could argue that Lyft is now where you’d expect a public company to be, where what you’re saying is, ‘This is the [total addressable market].’ Once a company is public, it’s much more, ‘These are our earnings, this is how our performance impacted our revenue.’ You could argue that Lyft is where Uber may end up having to go [in terms of how it calculates this figure].

TC: Riders use both apps, drivers use both apps. Do you ever see these companies merging? As you likely remember, they talked in 2014, Travis confirmed in an interview in 2016, but he said disagreements over pricing ultimately doomed the deal.

BT: I don’t even know if they could get through the FTC for approval if you add up their collective share in the rideshare marketplace. And now that they’re both public companies, the ability to challenge them will be harder unless Waymo or some other robo company tries taking away their market share.

TC: Do you see Uber making money at some point?

TC: Yeah. I think it may be the result of more and more partnerships around ridesharing in different markets. I also think they’ll be able to take the Uber Eats and Uber Freight concepts and keep building out other things from these. Eats gets into package delivery, for example. If all of those things come to fruition, Uber will be profitable.

TC: How many years did you advise Uber?

BT: I started in 2011, and finished in 2015.

TC: What are you proudest of?

BT: Even more than a particular market — because eventually we won all over the U.S. — it’s this notion that if you give people a really easy way to advocate for themselves, they’ll get involved. The notion that everyone is apathetic isn’t actually true, and we used that to fight taxis everywhere, including when Uber was not a valuable company and we were taking on the [much-deeper-pocketed] taxi industry.

Our thesis was right and the execution all-in-all worked, and it’s really one of the insights that’s now propelling the work in mobile voting that I’m doing. I’m operating on the assumption that if you increase turnout by making it easier and more convenient for people to engage in the process, politicians will change their behavior.

TC: Travis Kalanick is obviously a strong leader and seemingly stubborn, too. What was one suggestion you made to him that he didn’t take yet could have changed things for the company, in potentially a meaningful way?

BT: This wasn’t to him, but I suggested a few years ago that Uber provide benefits for all drivers. At the time, it wasn’t met with a lot of optimism, but I think the world is heading in that direction anyway, and I think they could have saved money by having a lower churn rate than what they have, as well as improved their optics and reputation.

TC: You have a lot of promising bets in your portfolio right now. Do you see any of these getting anywhere near the scale of Uber or is this a once-in-a-decade type company?

BT: I think something can. I hope something in my portfolio will. I think every VC will tell you that every day, they see deals with [total addressable markets] in the low trillions. The number of companies that can convert that into revenue [and reach an Uber-like valuation] is few and far between, but someone will pull it off, in some sector.

TC: The company is hitting the market next week. What are you doing to celebrate?

BT: When I sold a chunk of my shares to SoftBank — close to half — psychologically it had the impact [that I would otherwise experience next week]. You know, we were able to benefit from this thing. Anything I wanted to do could then happen. So it isn’t that it’s not a huge deal. I just think it would be 10 times more anxiety producing for me if that hadn’t happened.